Potassium Carbonate → (3-Amino-propyl)-methyl-carbamic acid isopropyl ester

HRID 870673Notes

Reaction equation

HRID 870673 reaction equation
[CH:1]([O:4][C:5](=[O:18])[N:6]([CH3:17])[CH2:7][CH2:8][CH2:9][NH:10]C(=O)C(F)(F)F)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH:1]([O:4][C:5](=[O:18])[N:6]([CH2:7][CH2:8][CH2:9][NH2:10])[CH3:17])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86696374Methyl-[3-(2,2,2-trifluoro-acetylamino)-propyl]-carbamic acid isopropyl ester

Product 1

HCID 61799490(3-Amino-propyl)-methyl-carbamic acid isopropyl esterYield 109.1%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A suspension of methyl-[3-(2,2,2-trifluoro-acetylamino)-propyl]-carbamic acid isopropyl ester (9.0 g, 33.15 mmol), and potassium carbonate [584-08-7] in 50% (v/v) methanol/water (200 mL) was stirred at ambient temperature, under N2 blanket for 17 h, filtered, and the filtrate evaporated to reduce its volume. The resultant aqueous product solution was place in a continuous extractor and extracted with ethyl acetate to 2d. The ethyl acetate extract was dried (CaSO4) and evaporated to afford 6.3 g of clear yellow oil. LRMS (ESI) m/z 175.1 [(M+H)]+, calc'd for C8H18N2O2: 174.24.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated
  3. extractionextracted with ethyl acetate to 2d
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried (CaSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-735979d8fea8492db74145ed2c54a2b0
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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